How to Tackle Hilton Head

Hilton Head Island in a nutshell: Vacationing families connecting—via scents, scenery, and seafood—with the second-largest barrier island on the East Coast. And while most of the 2.5 million annual visitors tend to come during warmer months, they miss out on what might be the island's best time of year. After Labor Day and before spring break, the humidity drops, traffic trickles off, crowds thin and temperatures average in the 60s. Folks toss on fleece pullovers to walk the 12 miles of beaches; ride fat-tired, single-speed cruisers along epic bike paths; and hunker down at cozy oyster roasts. Sound good? Grab the Low Country winter uniform—flip-flops, khakis, and light sweater—and come on out to Hilton Head.

Hilton Head is a 45-mile drive north from Savannah, GA, and 110 miles south of Charleston, SC. In the early 16th century, the French and Spanish attempted to settle this fertile land. Its live-oak forests and rich soil made it an agrarian paradise; the many waterways facilitated shipping; and the proximity to the Eastern seaboard made it a prime outpost. But local tribes didn't entirely welcome those early visitors. Finally, in 1663 British sea captain William Hilton successfully claimed the island for England, giving plantation life its start.

Today, Hilton Head Island is a funky mix. Historical sites are scattered among the resort-community-and-golf-course descendants of Sea Pines; hotels butt up against huge swaths of preserved land, while shopping and dining strips flood the interior. A four-lane road encircles the island, with hideaway developments shooting off it like spokes. And here and there, humble vegetable plots thrive next to multimillion-dollar digs and modest, slouchy cottages alike.

"This is the most relaxing vacation I've had with my family—ever," says a woman making her way across Broad Creek by kayak. "It's the first time we've ever just chilled out, relaxing on the beach, me reading and the kids shelling, and all of us trying new things."

To score that same experience, you'll need a strategy. Hilton Head has 250-plus restaurants and two dozen golf courses, so it's crucial to narrow your field of vacation vision. For a family-flavored getaway (the island's specialty), first pick a place to stay. If you're flying in, look for flights to the Savannah/Hilton Head International Airport. And on your way to the island, stock up at the Publix in neighboring Bluffton to avoid the weekend crowds at island grocery stores.

Next, come up with your dream menu of outdoor activities. Hotels and resorts offer daily tours; ask for schedules when you check in. Or try Outside Hilton Head for kayaking, boating, fishing and dolphin-cruising options. If you’re not staying at a resort with beach access, you can hit the sand at several public access points. The most popular one is Coligny Beach Park, with ample parking and a brand-new area with restrooms, showers and more.

As for getting around, either bring your own bicycles or rent from Hilton Head Bicycle Co. And for the ultimate Lowcountry experience, don't miss exploring the Sea Pines Forest Preserve. This 605-acre wilderness oasis combines jungle-like expanses of native evergreen palms, live oaks and wax myrtles with lagoons populated by cranes and alligators. Powdery dirt roads traverse the gently sculpted site. Pick up a map at the info center hutch and head off by foot, bike or car—or on horseback. For a trail ride, sign up with Lawton Stables.